1. “Keep Me In Your Heart” by Warren Zevon

Warren Zevon is best remembered for songs like “Werewolves of London”, “Lawyers, Guns and Money” and “Roland the Headless Thompson Gunner.” Sometimes people forget that, while Zevon’s biggest successes may have been his more detached songs, Zevon also wrote some fantastic intimate ballads, such as “Hasten Down the Wind” (made famous by Linda Ronstadt) and “Desperadoes Under the Eaves”. However, his masterpiece may be “Keep Me In Your Heart”.

In 2003, Warren Zevon had been diagnosed with terminal brain cancer, and was given only a short time to live. He set out to record his final album, The Wind, and invited many of his friends to perform with him on the album (you may recognize some of them in the video). However, the last song he recorded was “Keep Me In Your Heart”, the last plea of a dying man to not be remembered forever, but just to keep his memory in their hearts for “a while”. It is perhaps the most honest look at the final thoughts of a man facing his own demise. Zevon had regularly recorded songs about death and dying during his career, but none of them have the power of “Keep Me In Your Heart”.

2. “Tears in Heaven” by Eric Clapton

One of Clapton’s most successful songs comes from one of the most tragic chapters of his life. Clapton wrote the song following the death of his four-year-old son, who fell out the 53rd story window of a friend’s apartment building in New York City. This followed the death of his manager and two members of his road crew, along with Stevie Ray Vaughan in a helicopter crash.

Clapton, along with songwriter Will Jennings (who had previously worked with Steve Winwood and would go on to write “My Heart Will Go On”) has been contracted to work on the soundtrack to the movie Rush. After recording a song for the movie, Clapton approached Jennings about helping him complete a song about his son which would also go on the soundtrack. Hesitant at first, Jennings eventually agreed, flushing out the verses of the song for Clapton. Clapton stopped performing this song, as well as “My Father’s Eyes” in 2004, saying he could no longer evoke the emotion needed to perform them.

3. “Nothing Compares 2 U” by Sinéad O’Conner

Originally a song written by Prince for his side project The Family, the song became a huge hit when it was covered by Irish singer Sinéad O’Conner. A song about heartbreak and the emptiness that dwells inside us after a relationship ends struck a chord with audiences and launched O’Conner into stardom.

O’Conner cited the lines “All the flowers that you planted, mama/In the backyard/All died when you went away” as the emotional crux of the song for her, as she had a complex relationship with her mother. The raw emotion comes through in a music video which consists largely of a closeup of O’Conner as she sings the song, letting her convey the raw emotion directly to the audience.

4. “Hallelujah” by Jeff Buckley

“Hallelujah” is a song that can be triumphant or bittersweet, lovely or chilling depending on the artist, the verse, or the mood of the listener. Leonard Cohen struggled with the song for years until John Cale asked him for the lyrics—and Cohen sent him 15 pages. Cale reduced the song, but it wasn’t until Buckley covered it for his lone complete album Grace that the song reached it’s true potential.

Buckley’s tragic death (and the much later mainstream acceptance of his music) amplifies the dark beauty of Cohen’s lyrics. John Legand described Buckley’s version as “one of the most beautiful pieces of recorded music I’ve ever heard.” The song has surged in popularity in recent years due to appearances in movies and television shows, as well as cover versions on The X-Factor and American Idol.

5. “Casimir Pulaski Day” by Sufjan Stevens

Sufjan Stevens “Casimir Pulaski Day” drops the line “cancer of the bone” in the first verse and doesn’t let up throughout the song. The story is one from Stevens’ youth, when he had his first experience with death with a young friend. He recalls the confusion, the angry, the lack of understanding that all young people go through with a rarely seen simplicity.

“Casimir Pulaski Day” recalls specific moments—both good and bad that lead up to the death of his young friend, creating a haunting a very real portrait that invite the listener to experience the grief with him. The song ends with a light melody, but not before the narrator questions the wisdom of the Lord for his taking, and his now questionable faith in God.

6. “I Can’t Make You Love Me” by Bonnie Raitt

Co-Written by former Pro-Bowl Defensive Tackle Mike Reid and Allen Shamblin, the song tells the story of unrequited love and the heartbreak within. Backed by Brunce Hornsby on the keys, Raitt’s version was recorded in one take in the studio, because Raitt couldn’t recapture the raw emotion of the initial performance. It’s a notoriously hard song to perform, not just because of the emotion involved, but also the difficult lyrics.Raitt has described the song as the hardest to perform in her catalog.

“It’s almost a sacred moment when you share that, that depth of pain with your audience. Because they get really quiet, and I have to summon … some other place in order to honor that space.”

7. “Hurt” by Johnny Cash

When Johnny Cash asked Nine Inch Nails’ Trent Reznor for permission to cover “Hurt”, Reznor was skeptical at first about the project, worried that it would be too gimmicky. However, when Reznor first saw the music video he immediately became a huge fan of Cash’s version, eventually stating that “That song isn’t mine anymore”.

Cash’s version, radically different from the Nine Inch Nails version of the song from “The Downward Spiral”, yet retaining the same lyrics, shows the power of music and a well written song as two artists as different as Reznor and Cash can come together to create a piece of music that both brilliantly haunting and powerfully emotional.

8. “Brick” by Ben Folds Five

At the time, Ben Folds Five was known for playing up-tempo piano rock songs, so “Brick” seemed to come out of nowhere for a group that was known for a much lighter fare. The group had a hard time working the song into their live shows, as it didn’t match anything else in their catalog at the time. However, it would eventually become their fourth single off Whatever and Ever Amen and become their most successful song.

Folds wrote the song about an experience he had in high school, when he accompanied his girlfriend to get an abortion. He struggled with the song for years, eventually discovering the song was too literal. For several years after the release of the song he did not discuss the songs inspiration, wanting the song to speak for itself. He eventually began to introduce the song with the story at concerts as a solo artist.

9. “The Boxer” by Simon and Garfunkel

Simon and Garfunkel regularly explore an area of darkness and sadness, from “I am a Rock” to “The Sounds of Silence”. “The Boxer” is their saddest and most powerful song, punctuated by a chorus that simply goes “Lie-lie-lie.” Simon admits that he simply could not think of the words to put in there, but the absence of words makes the song even more powerful.

The titular boxer doesn’t show up until the third verse, and he is covered in cuts and bruises. He threatens to leave if he continues to be punished, yet we all know the calls are futile. The song took on special meaning for Simon later in life, and has regularly been used as a solemn ballad in hard times.

10. “The Freshmen” - The Verve Pipe

90’s alt-rockers The Verve Pipe one-hit was nevertheless a big one, as “The Freshman” remains as a testament to the power of modern rock at the time. To song, about a moment in youth where a freshmen in suddenly met with the reality of adulthood, is a stunning look at the internal struggles of a couple in the midst of disaster.

At the time of the writing and release of the song, it was stated that it was about the guilt felt by lead singer Brian Vander Ark’s following the suicide of his ex-girlfriend. Vander Ark has since recanted that story, claiming it was poetic license. However, the power of the song and the emotions in the lyrics make it a standard for 90’s modern rocks and one of the most effective rock ballads of that decade.

Obviously this is just the tip of the iceberg as far as sad songs go, and there are many great sad songs that didn’t make the list. Please add your own personal favorite sad songs in the comment section below.